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Hudson Valley Escapes: Ossining

August 12, 2008 at 12:00 PM | 0 Comments

If you only know Ossining as New York's funniest-sounding place, or even if you only know it as the home of Don Draper from "Mad Men," you're missing out on one of the best just-beyond-NYC small towns.

Set right on the Hudson, this quiet village was originally called Sing Sing, but changed its name in 1901 after a boycott of goods made at nearby Sing Sing Prison started to hurt town businesses as well. Today, Sing Sing Prison is still around, and Ossining is a sleepy little village with a quaint Main Street strip surrounded by an impressive array of wilderness.

Everything in Ossining is close enough to find in a quick walk or drive, but what follows are a few of our favorites.

Where to Eat: It's worth driving a little off the main strip to Wobble Café on Campwood Road for a weekend breakfast of fresh fruit crepes, eggs poaches in creamed arugula and mounds of home fries.

Where to Play Outside: New York's delicious drinking water comes from upstate, originally via the Old Croton Aqueduct, an 19th-century masonry tunnel. No longer in operation, the path over the aqueduct is now a 26-mile-long state park with some of the area's best hiking trails. You can even enter part of the aqueduct itself for a historical tour.

Where to Play Inside: Sing Sing itself is still a functioning jail, so don't go looking for a guided tour. But the "museum" at the Ossining Community Center offers a look into the prison's history, complete with a replica electric chair.

Where to Stay: Ossining isn't really blessed with accommodations. If you're staying the weekend, head just up the road to Croton-on-Hudson, where the Alexander Hamilton House is a cute, waterfront B&B.

Getting There: Ossining is 40 minutes from Grand Central on Metro-North, and there are usually taxis and Zipcars at the train station.

Related Stories:
· Wobble Cafe [Official Site]
· Friends of the Old Croton Aqueduct [Official Site]
· Alexander Hamilton House [Official Site]
· Hudson Valley Escapes coverage [Jaunted]

[Photo: mysticchildz]

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